10 Of The Most Intimate Questions You Could Ask Someone You’re Dating

We’ve been around the block once before when it comes to dating and so we have a really good grasp on the kinds of questions we need to be asking in order to get to know each other better. Of course, it’s through deep questions and discussions wherein we can really get to know more about the person we’re dating. But there is always this unspoken rule about the boundaries of intimate questions that come up during dates. What kinds of questions are off-limits when it comes to dating?

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When is it okay for you to ask these questions to someone that you’re seeing? Well, only you can really gauge for yourself when the appropriate time to ask these questions would be. But just so you know, here are some of the most intimate questions that you could ever ask someone that you’re dating.

1. Are you still a virgin?

Of course the details of someone’s sex life are always going to be intimate. And so if you’re going to choose to ask your partner this question, make sure that you are at a point in your relationship where it’s okay for you to be talking about stuff like this. Remember that not every person is up for talking about their sex lives right away.

2. Do you smoke?

Smoking just isn’t as popular as it used to be. Granted, there are still so many smokers out there, but given the gradual decline of its popularity, a lot of people have resorted to being closet smokers. They will want to hide this disgusting habit from the public because they don’t want to be judged for their addiction.

3. Do you have a criminal record?

At first glance, you would think that anyone would have the right to ask this question to anyone they’re dating. It’s a security issue. Of course you wouldn’t want to be dating someone who is known to have criminal tendencies. However, you also run the risk of asking a perfectly innocent man whether he is a criminal. That can make for some very awkward dinner conversation.

4. Have you ever cheated before in relationships?

No one in their right mind would ever want to be cheated on in a relationship. And so it would make sense for you to not want to date someone who has a history of cheating. However, when you ask this question to the person that you’re dating, it would come off as if you’re accusing them of possessing the character traits of a cheater. You have to be very careful whenever you choose to tread this line.

5. How many people have you had sexual encounters with?

Again, not everyone is going to be comfortable with talking about their sexual histories. You have to be very careful whenever you choose to inquire about a person’s sexual encounters because if they’re not comfortable with talking about it, then you run the risk of coming off as snoopy. You don’t want to be seen as the person who is always sticking your nose into places you don’t belong.

6. What’s your stance on monogamy?

Of course, you want some sort of insurance when it comes to the relationship. You want to make sure that you won’t end up being just one of the many that your partner could be dating. But again, you risk looking like someone who is overly paranoid when you ask your partner this question. Also, your partner may feel bad that you are essentially suspecting them of being polygamous even though they really aren’t.

7. Do you have a good credit rating?

Finances are always tricky situations. Whenever you want to get serious with someone in a relationship, eventually you are going to have to open up about your financial situations. However, if you ask this question too early in a relationship, you will risk coming off as very materialistic and cold. Money is an important subject, but very careful about this question.

8. Are you dealing with any serious mental health issues?

This is one of those high-risk, low-reward kind of situations. Yes, if your partner has a mental issue, you would want to do yourself a favor and find out about it early on. But if it turns out that your partner doesn’t have a mental issue when you ask this question, then you are potentially triggering something that is very deep.

9. Do you want kids in the future?

Kids are always a sensitive issue. In very rare cases, it would be okay to ask this question early on in the dating phase of your relationship. However, for the most part, you should really hold off until you and your partner are really comfortable about discussing the future together.

10. Do you have any diseases I need to know about?

Again. Sensitive topic. A person’s sexual history is always going to be taboo. But hey, you don’t want to risk contracting a disease from this person, right? Better to be safe than sorry.

Talk to me

What’s the most intimate question you’ve been asked? Talk to me in the comments below!